Abdul Osman scored the winning spot-kick after Nathan Eccleston missed his for Liverpool. Michael Jacobs looked to have sealed an historic win for Northampton in extra-time before David Ngog forced the match to penalties at 2-2. Milan Jovanovic’s opener was cancelled out by Billy McKay as the sides were level after 90 minutes.

Shola Ameobi’s last-gasp winner secured a surprise 4-3 win for Newcastle to send Chelsea crashing out as well. Nicolas Anelka’s two late goals looked to have been enough to force extra-time at Stamford Bridge, but Ameobi’s glancing header from Jonas Gutierrez’s cross sealed an impressive win for the Magpies.

Chelsea looked set for a comfortable victory after Patrick van Aanholt scored his first senior goal after six minutes, but Nile Ranger, who was at fault for the opener, went some way to atone for his mistake when he equalised shortly before the half-hour mark. Just moments later Ryan Taylor’s free-kick put the visitors ahead, and Ameobi scored his first to give Newcastle a 3-1 lead shortly after half-time.

To add insult to injury, Chelsea lost Salomon Kalou to a hamstring injury, and when Yossi Benayoun hobbled off, Chelsea had no option but to continue the match with ten men with Carlo Ancelotti having already employed all three of his substitutes. But two late goals from Anelka, including a casual penalty with three minutes remaining, set up a tense few minutes, but Ameobi wrapped up a memorable victory for Newcastle with his late winner.

Holders Manchester United were forced to come from behind to beat underdogs Scunthorpe5-2. Josh Wright’s long-range strike gave the home side a deserved lead, but it proved to be shortlived as Darron Gibson beat the offside trap to lob Joe Murphy from Chris Smalling’s long ball just four minutes later.

After his role in United’s opening goal, it was Smalling’s turn to get on the scoresheet, netting his first senior United goal to put the visitors ahead. Scunthorpe could have clawed their way back into the match when Kuszczak palmed Jonathan Forte’s long-range effort away, but the ball bounced just in front of his right post before spinning wide.

Scunthorpe battled valiantly, but the gulf in class and fitness began to appear, and the game soon ran away from them with two goals from Michael Owen and one from Park Ji-Sung before Martyn Woolford’s 90th-minute consolation.

Ashley Young scored two goals in three minutes as Aston Villa came from behind to beat Blackburn3-1 at Villa Park. Gael Givet gave Blackburn the lead after 34 minutes before Emile Heskey equalised on the hour mark. And Young’s double 13 minutes from time secured victory for Gerard Houllier on his first game in charge of Villa.

West Brom also came from behind to beat Manchester City2-1. Jo’s left-footed strike put the visitors ahead on 19 minutes, but two goals in quick succession from Gianni Zuiverloon and Simon Cox sent Roberto Mancini’s men crashing out.

Charles N’Zogbia’s 90th-minute strike sealed a late 2-1 win for Wigan at home to Preston North End. Wigan looked to be heading out of the competition after Keith Treacy put the Championship side ahead after 23 minutes, but Jordi Gomez’s 87th-minute equaliser looked to have been enough to force extra-time before N’Zogbia spared Roberto Martinez’s men’s blushes.